Arylation, alkylation, reduction, and pyrolysis of 1h-1-methylindeno[2,1-b]pyridine

Nucleophilic substitution (phenylation with phenyl lithium) of 1H-1-methylindeno[2,1-fa]pyridine occurred at the C(2) and C(4) positions, and electrophilic substitution (methylation and benzylation with halogen derivatives) at C(9). Reduction of the starting anhydrobases gave 1-methyl-1,2,3,9a-tetrahydro-1-azafluorene, and pyrolysis gave 1-azafluorene and 1-azafluorenone. © 1987 Plenum Publishing Corporation.